Lynn Yaeger – a name synonymous with style, singularity and self-awareness – will receive the Media Award in Honor of Eugenia Sheppard at this year’s CFDA Awards Monday evening. The quirky industry icon – clad in Simone Rocha-ruffles toting a covetable collection of handbags –once stood in the mailroom of the Village Voice before making a name for herself as their fashion reporter and going on to contribute to Vogue, The New York Times and The New Yorker. It was with one swift pitch and a subsequent call from Cosmo that Yaeger would embark on a career that now comes to be saluted by the CFDA.

Brave and courageous in her willingness to push sartorial boundaries, she is just as brilliant in her way with words. We took a moment with the Media Award-honoree to discuss how the digital age has reshaped the industry landscape and her most recent fashion indulgences. Spoiler alert: she’s a serial sale shopper and has a soft spot for Balenciaga.

You are perhaps one of the greatest authorities in fashion and one of the most celebrated figures of personal style today. To what can you attribute your unique sense of style?I never thought normal clothes looked good on me! I guess I always had some other vision in my mind, and I was inspired early on by things like vintage ballet tutus, 1920s fashion and makeup, even doll clothes.

Do you think that it can be learned? Acquired? Passed down? 

Definitely learned and acquired! I have ripped off lots of people, alive and dead. Not sure about passed down…

What is your fondest memory of fashion as a child? How did growing up in Long Island influence you? 

Well, as a child I always loved shopping, and my parents were nice enough to indulge me. But I hated Long Island—the only good thing about it is that it is fairly near NYC. (Who could believe that Massapequa is on the same strip of land as East Hampton? It boggles the mind.)

Can you define “fashion” in three words? 

Nope!

Many are quick to dismiss clothing as materialistic, shallow, trivial. Meanwhile, others bask in its allowance of creativity and self-expression. How do you perceive it? Is there a line where it crosses over to the ‘dark side’?

I believe in a very expansive view of fashion, and I don’t think the impulse to decorate oneself is shallow or trivial. I am interested in all kinds of fashion—how private school kids customize their uniforms, how trans kids look amazing with no money, how trends and ideas drift up from the street and onto the runways, rather than the other way around.

You studied sociology at Fordham before switching to art history, and then political economy as a graduate student at The New School – never fashion, nor journalism. Where did you find your voice? Pun unintended.

Well I was not a very good student, regardless of the field. The only thing I was ever any good at was writing—and I am one of the few writers I know of who actually likes writing.

Alongside being an acclaimed editor, journalist and Vogue contributor (presented with this year’s CFDA Media Award in Honor of Eugenia Sheppard), you’re also a street style icon. How have you seen today’s street-style movement alter the fashion landscape? 

I don’t know really, I have always dressed like this, long before there was street style or social media or even the internet. I don’t really understand people who dress up for cameras—I dress like this even when I am taking out the trash.

What about the media landscape? How have you found the relationship between fashion and media to have shifted throughout the digital age? 

Everything has changed, but I think it’s good. Now everyone can see fashion shows on the internet five minutes after they happen, and everyone can weigh in with his or her opinion, and I think that’s pretty great.

How would you like to see the industry change, if at all?

Easy question—more diverse please! More inclusive! Really mean it when you say you are open to all kinds of fashion and beauty.

Lastly, can you describe your most recent purchase in excruciating detail?

Ok well, there is currently the case of the two Balenciaga bags bought on Yoox—the Paris souvenir one from last season and the blanket flower one from the year before. Now what do I do? Keep them both? (I am the queen of the serious markdown.) Oh, and there is also a Simone Rocha skirt in the mail arriving shortly…